Reaktion #317513

Reaktionsgleichung

tris(2-methylphenyl)phosphine

2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester

tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

potassium carbonate

→

(E)-2-(2,6-dichlorobenzamido)-5-[4-(4-hydroxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester

Ausbeute 5.9%

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the reaction solution to room temperature
2. 2
   Waschenthe solution was washed 3 times with water
3. 3
   Trocknenby drying the organic layers over anhydrous sodium sulfate
4. 4
   SonstigeAfter removing anhydrous sodium sulfate
5. 5
   Filtrationby filtration
6. 6
   Einengenthe filtrate was concentrated
7. 7
   SonstigeThe residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/4)

Vorschrift

Under an argon atmosphere, palladium acetate (4.7 mg) and tris(2-methylphenyl)phosphine (6.1 mg) were added to a suspension of 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (60.4 mg), tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (60.8 mg) and potassium carbonate (41.5 mg) in DMF (4 ml), and the resulting mixture was stirred at 80° C. for 6 hours. After cooling the reaction solution to room temperature, ethyl acetate was added thereto and the solution was washed 3 times with water and once with saturated brine, followed by drying the organic layers over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/4) and thereafter by thin layer chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate=1/1) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(4-hydroxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester (5.6 mg).

Quelle